Process for the preparation of defined functional lactic acid oligomers

Abstract

A process for the manufacture of a block copolymer includes a reaction of a lactide monomers in the presence of a catalyst with a polymer to form the block copolymer having a lactic acid chain, wherein a polymer selected from polypropylene, polyethylene, polysiloxane, polybutylene succinate, polytrimethylene carbonate, polyester, polyether, polystyrene, polyisoprene, polycarbonate, polyalkylenecarbonate, polyvinyl alcohol, polyurethane, or polyacrylate; and wherein the polymer contains n number of OH and/or NH2 group(s), n is an integer greater than or equal to 1 and Moles ⁢ ⁢ of ⁢ ⁢ Lactide ( Moles ⁢ ⁢ of ⁢ ⁢ Compound * n ) ≤ 70 , and the reaction is performed at a temperature of at least 70° C. The process includes step of quenching of the reaction in order to form the lactic acid chains consisting of 70 or less of the lactide monomers, and the quenching agent is an acid chloride having a formula of Cl—CO—R 9 , wherein R 9 is 1-pentenyl or aminoethyl.

The invention claimed is: 
     
       1. A process for the manufacture of a block copolymer comprising:
 contacting lactide monomers in the presence of a catalyst with at least one compound to form the block copolymer comprising a lactic acid chain; 
 wherein each compound is a polymer selected from the group consisting of polypropylene, polyethylene, polysiloxane, polybutylene succinate, polytrimethylene carbonate, polyester, polyether, polystyrene, polyisoprene, polycarbonate, polyalkylenecarbonate, polyvinyl alcohol, polyurethane, and polyacrylate; 
 wherein each polymer contains n number of OH and/or NH 2  group(s), wherein n is an integer greater than or equal to 1, wherein 
 
       
         
           
             
               
                 
                   Moles 
                   ⁢ 
                   
                       
                   
                   ⁢ 
                   of 
                   ⁢ 
                   
                       
                   
                   ⁢ 
                   Lactide 
                 
                 
                   ( 
                   
                     Moles 
                     ⁢ 
                     
                         
                     
                     ⁢ 
                     of 
                     ⁢ 
                     
                         
                     
                     ⁢ 
                     Compound 
                     * 
                     n 
                   
                   ) 
                 
               
               ≤ 
               70 
             
           
         
         wherein reaction is performed at a temperature of at least 70° C.; 
         quenching the reaction of formed lactic acid chains consisting of 70 or less of the lactide monomers, wherein the quenching agent is an acid chloride having a formula of Cl—CO—R 9 , wherein R 9  is 1-pentenyl or aminoethyl, and wherein each lactic acid chain is bonded to one of the polymers; 
         wherein 
       
       
         
           
             
               
                 
                   
                     Mn 
                     ⁡ 
                     
                       ( 
                       
                         lactic 
                         ⁢ 
                         
                             
                         
                         ⁢ 
                         acid 
                         ⁢ 
                         
                             
                         
                         ⁢ 
                         oligomer 
                       
                       ) 
                     
                   
                   - 
                   
                     Mw 
                     ⁡ 
                     
                       ( 
                       compound 
                       ) 
                     
                   
                 
                 n 
               
               ≤ 
               
                 10100 
                 ⁢ 
                 
                   
                       
                   
                   ⁢ 
                   
                       
                   
                 
                 ⁢ 
                 g 
                 ⁢ 
                 
                   / 
                 
                 ⁢ 
                 mol 
               
             
           
         
         wherein Mn(lactic acid chain) is measured by size exclusion chromatography, and wherein n is the number of OH and NH 2  groups present in the compound. 
       
     
     
       2. The process according to  claim 1 , wherein said process is performed without solvent. 
     
     
       3. The process according to  claim 2 , wherein said process is performed at a temperature of 110° C. to 190° C. 
     
     
       4. The process according to  claim 1 , wherein the catalyst is an organometallic catalyst. 
     
     
       5. The process according to  claim 1 , wherein said catalyst has general formula:
   M(Y 1 ,Y 2 , . . . Y p ) q , 
 wherein M is a metal selected from the elements of columns 3 to 12 of the periodic table of the elements, as well as the elements Al, Ga, In, Tl, Ge, Sn, Pb, Sb, Ca, Mg and Bi; 
 wherein Y 1 , Y 2 , . . . Y p  are each substituents selected from C 1-20  alkyls, C 6-30  aryls, C 1-20  alkoxys, C 6-30  aryloxys, other oxides, carboxylates, and halide groups as well as elements of group 15 and/or 16 of the periodic table; 
 wherein p and q are integers between 1 and 6. 
 
     
     
       6. The process according to  claim 5 , wherein the reaction is performed at a temperature of at least 140° C. 
     
     
       7. The process according to  claim 1 , wherein n is at least 2. 
     
     
       8. The process according to  claim 1 , wherein said compound is a polymer that is selected from the group consisting of: polypropylene, polyethylene, polysiloxane, polybutylene succinate, polytrimethylene carbonate, polystyrene, polycarbonate, polyalkylenecarbonate, polyvinyl alcohol, and polyurethane, wherein the polymer contains n number of OH and/or NH 2  group(s), and wherein n is an integer greater than or equal to 1. 
     
     
       9. The process according to  claim 1 , wherein the compound is a polymer selected from the group consisting of: polypropylene, polyethylene, polysiloxane, polybutylene succinate, polytrimethylene carbonate, polycarbonate, polyalkylenecarbonate, polyvinyl alcohol, and polyurethane, wherein the polymer contains n number of OH group(s), and wherein n is an integer greater than or equal to 1.